I [25F] am hooking up with an old friend [27M] on a semi-regular basis. Do I need to tell my once-estranged, now close-again friend [25F], who he unenthusiastically hooked up with a few times three years ago, that we’re currently hooking up?

This is a throwaway account, as one of the parties involved (Sam) knows my main handle.

Ok, bit of backstory. Late 2015/early 2016 I was sharing a house with my friend Leonie [25F, as mentioned in title, 22 at time of these events]. Our other housemate was interstate for a few months, so we bring in this subletter - we’ll call him Sam [27M, 24 at this point]. Leonie joked that she’d matched with him on Tinder. He was VERY good looking and, it proved, a pretty warm and interesting guy. He and I got along well. I had a very small crush which I didn’t fan the flames of, as I was in a (ultimately not great) LTR.

Around late January these two started hooking up. Leonie was pretty into Sam; not so much the other way around (my perception at the time of events was that he was just a more passive guy, and that he was ok with everything but not pushing for it). I don’t know exact details but I think they had sex a few times, plus some public making out. He moved out when our old housemate moved back in.

Shortly after, Sam started dating a girl he met on Tinder, Nella [24F, 21 at this time]. Leonie was pissed but never copped to being mad to his face. Sam and I stayed in touch; my then-boyfriend Dean [24M, 22 then] and I went on a double date with him and Nella, and then we all went to a few parties together shortly after.

Later in 2016 Leonie and I had a big falling out, unrelated to Sam but related to being bad housemates; we completely stopped speaking. During this time, Dean and I remained close with Sam and Nella. I found out around that Sam had no warm feelings toward Leonie - he felt he had been pressured into hooking up with her, including some weird usey stuff where she was feeling him up in public and kissing him pointedly in front of her ex. I went overseas for 6 months; when I came back, Dean and I moved in together, and Sam and Nella morphed back into our extended social network.

In mid-2017, Dean and I broke up. It was the difficult end of a difficult relationship. Sam and Nella actually gave me considerable support through this time - while I had other closer friends, they would take me out for dinner and invite me to all their parties. They were great fun to hang out with, but during this time, I began to notice a disturbing pattern where Nella would do some dodgy stuff to Sam - such as stonewalling him in public. This struck me as pretty abusive and I would tentatively try and see if Sam was ok - without straight out going “your girlfriend is being a creep”. He generally seemed embarrassed about these occurrences, although I think he certainly had no reason to be.

Over the next year Sam, Nella and I essentially maintained our friendship - as much as I wanted to subtly show that I was there if Sam wanted to talk, I knew from experience with Dean that sometimes there’s no telling someone that they’re in an unhealthy relationship (I didn’t want to hear it with Dean). During this time, I found out they were in an open relationship. In mid-late 2018 I had a disagreement with Sam - he started seeing a then-pal of mine who I thought was going into it with the presumption of monogamy. We drifted; I also drifted from Nella, who I got the impression wasn’t happy with Sam seeing this particular person either. Meanwhile, Leonie and I crossed paths again working on a project, and slowly started to put pieces together back toward a friendship.

I had also started dating someone else in late 2017, who I dated for slightly over a year and broke up with in late January this year (2019). Shortly after this ended, Leonie and I made up properly, and started hanging out like normal friends again. I found out around the same time that Nella was moving interstate; I presumed Sam was going with her and thought it was time to mend fences if he was leaving town. We caught up for lunch and had a good DnM; I apologised for being out of line with the pal situation; he revealed he wasn’t sold on following Nella and didn’t know if he could find decent work in her new city, but was worried about her mental health if he didn’t. I tentatively suggested that he had to do what felt right for him.

About a month after we hung out, I started getting Instagram DMs from Sam on a pretty regular basis - story replies mostly. We’d always messaged a bit, but this seemed more frequent than usual - every second day or so - with some semi sexual jokes. We joked about going to the movies together, and then made plans to actually do so (as it was a movie of a type not many people we knew appreciated). Shortly before we made a concrete time to watch the movie together, he mentioned that he’d broken up with Nella. I treated it like I would a girlfriend who’s broken up with her partner - I just said I’d bring plenty of ice cream.

We hung out at his and watched the movie - nothing happened. About a month later, with lots of DMs in between, we decided to watch another movie. This time, nothing DIDN’T happen. The thought had definitely crossed my mind that we might hook up, but I had written it off because of all the history, the fact that we were friends, and honestly the fact that he’s really hot and I thought I had to be misinterpreting the situation. Plus I’d had enough experience with one night stands that I idly figured even if it happened, it’d be a bust and we’d try and forget it ever had happened. This couldn’t be further from what happened. It was phenomenal and it was pretty clear we both wanted it to happen again - in fact a few days afterward he was making reference to us having “months” to make different seasonally appropriate drinks when we hang out.

This happened at the start of the month. We’ve since “hung out” twice and had copious saucy message exchanges. I am intentionally just going with the flow, enjoying the moment, being safe, having an absolutely fantastic time, and do not expect a monogamous romantic relationship to necessarily come out of this. Some aspects of what’s happening do suggest it’s not a purely sexually based thing (such as him suggesting we could hang out without hooking up, and some flirting that I consider more cute than sexy - and yes, he definitely knows I’m fine with dirty talk, so it’s not just him being considerate), but I’m not digging too much at this stage to see whether that’s just our friendship staying on the table or whether he wants it to be more romantic. For many reasons, I feel like pushing to define the relationship is not the right path right now.

However, something is playing on my mind - Leonie. She and I are very close these days, and at the moment, I’m concealing what’s happening with Sam. I am conflicted as to whether I should tell her.

On the one hand - I don’t even know whether this thing is going to become any more serious; he might feel uncomfortable about me revealing it to her due to the very new nature of what’s happening, plus the fact that he felt uncomfortable about their hookup even at the time and doesn’t like her; she might be pissed, and end our friendship or abuse him or me or make the whole thing public, which otherwise would not be on the cards. I also kind of feel like telling her when the whole thing is pretty sexually focused currently might come off as rubbing it in her face, and I’m worried about trying to define a situation to her that I haven’t even defined with him or myself.

On the other hand, she’s my friend; I value our rebuilt and (until now) open and honest relationship, and I know I would feel gutted and also suspicious if a friend kept a secret like this from me for too long, particularly someone I trusted to be real with me. She does also have a happy long term partnership these days, so I wonder if that might mitigate things - but then I remember how much she resented Nella, and Nella wasn’t her friend. But then again, that was three years ago. But then again - I’m her friend. I’m just not sure what I should do.

Ideally, this thing continues naturally, and Leonie is chill. Is there a way I can achieve that, or do I just cover it up completely, or do I blow it up completely with no attachment to outcome? Do I tell Sam before I tell Leonie or will that make things weirder?

TL;DR I’m hooking up pretty consistently with an old friend Sam, who over 3 years ago hooked up with my friend Leonie, who caught feels at the time but is now in an LTR. Sam has no warm feelings towards Leonie and views their hookup as a mistake at best. Sam and I stayed mostly friends over the next few years while Leonie and I completely ended, then completely reforged, our friendship. Do I owe it to Leonie to tell her I’m hooking up with Sam, and if so, how?

Submitted June 25, 2019 at 12:17AM

This is a throwaway account, as one of the parties involved (Sam) knows my main handle.Ok, bit of backstory. Late 2015/early 2016 I was sharing a house with my friend Leonie [25F, as mentioned in title, 22 at time of these events]. Our other housemate was interstate for a few months, so we bring in this subletter - we’ll call him Sam [27M, 24 at this point]. Leonie joked that she’d matched with him on Tinder. He was VERY good looking and, it proved, a pretty warm and interesting guy. He and I got along well. I had a very small crush which I didn’t fan the flames of, as I was in a (ultimately not great) LTR.Around late January these two started hooking up. Leonie was pretty into Sam; not so much the other way around (my perception at the time of events was that he was just a more passive guy, and that he was ok with everything but not pushing for it). I don’t know exact details but I think they had sex a few times, plus some public making out. He moved out when our old housemate moved back in.Shortly after, Sam started dating a girl he met on Tinder, Nella [24F, 21 at this time]. Leonie was pissed but never copped to being mad to his face. Sam and I stayed in touch; my then-boyfriend Dean [24M, 22 then] and I went on a double date with him and Nella, and then we all went to a few parties together shortly after.Later in 2016 Leonie and I had a big falling out, unrelated to Sam but related to being bad housemates; we completely stopped speaking. During this time, Dean and I remained close with Sam and Nella. I found out around that Sam had no warm feelings toward Leonie - he felt he had been pressured into hooking up with her, including some weird usey stuff where she was feeling him up in public and kissing him pointedly in front of her ex. I went overseas for 6 months; when I came back, Dean and I moved in together, and Sam and Nella morphed back into our extended social network.In mid-2017, Dean and I broke up. It was the difficult end of a difficult relationship. Sam and Nella actually gave me considerable support through this time - while I had other closer friends, they would take me out for dinner and invite me to all their parties. They were great fun to hang out with, but during this time, I began to notice a disturbing pattern where Nella would do some dodgy stuff to Sam - such as stonewalling him in public. This struck me as pretty abusive and I would tentatively try and see if Sam was ok - without straight out going “your girlfriend is being a creep”. He generally seemed embarrassed about these occurrences, although I think he certainly had no reason to be.Over the next year Sam, Nella and I essentially maintained our friendship - as much as I wanted to subtly show that I was there if Sam wanted to talk, I knew from experience with Dean that sometimes there’s no telling someone that they’re in an unhealthy relationship (I didn’t want to hear it with Dean). During this time, I found out they were in an open relationship. In mid-late 2018 I had a disagreement with Sam - he started seeing a then-pal of mine who I thought was going into it with the presumption of monogamy. We drifted; I also drifted from Nella, who I got the impression wasn’t happy with Sam seeing this particular person either. Meanwhile, Leonie and I crossed paths again working on a project, and slowly started to put pieces together back toward a friendship.I had also started dating someone else in late 2017, who I dated for slightly over a year and broke up with in late January this year (2019). Shortly after this ended, Leonie and I made up properly, and started hanging out like normal friends again. I found out around the same time that Nella was moving interstate; I presumed Sam was going with her and thought it was time to mend fences if he was leaving town. We caught up for lunch and had a good DnM; I apologised for being out of line with the pal situation; he revealed he wasn’t sold on following Nella and didn’t know if he could find decent work in her new city, but was worried about her mental health if he didn’t. I tentatively suggested that he had to do what felt right for him.About a month after we hung out, I started getting Instagram DMs from Sam on a pretty regular basis - story replies mostly. We’d always messaged a bit, but this seemed more frequent than usual - every second day or so - with some semi sexual jokes. We joked about going to the movies together, and then made plans to actually do so (as it was a movie of a type not many people we knew appreciated). Shortly before we made a concrete time to watch the movie together, he mentioned that he’d broken up with Nella. I treated it like I would a girlfriend who’s broken up with her partner - I just said I’d bring plenty of ice cream.We hung out at his and watched the movie - nothing happened. About a month later, with lots of DMs in between, we decided to watch another movie. This time, nothing DIDN’T happen. The thought had definitely crossed my mind that we might hook up, but I had written it off because of all the history, the fact that we were friends, and honestly the fact that he’s really hot and I thought I had to be misinterpreting the situation. Plus I’d had enough experience with one night stands that I idly figured even if it happened, it’d be a bust and we’d try and forget it ever had happened. This couldn’t be further from what happened. It was phenomenal and it was pretty clear we both wanted it to happen again - in fact a few days afterward he was making reference to us having “months” to make different seasonally appropriate drinks when we hang out.This happened at the start of the month. We’ve since “hung out” twice and had copious saucy message exchanges. I am intentionally just going with the flow, enjoying the moment, being safe, having an absolutely fantastic time, and do not expect a monogamous romantic relationship to necessarily come out of this. Some aspects of what’s happening do suggest it’s not a purely sexually based thing (such as him suggesting we could hang out without hooking up, and some flirting that I consider more cute than sexy - and yes, he definitely knows I’m fine with dirty talk, so it’s not just him being considerate), but I’m not digging too much at this stage to see whether that’s just our friendship staying on the table or whether he wants it to be more romantic. For many reasons, I feel like pushing to define the relationship is not the right path right now.However, something is playing on my mind - Leonie. She and I are very close these days, and at the moment, I’m concealing what’s happening with Sam. I am conflicted as to whether I should tell her.On the one hand - I don’t even know whether this thing is going to become any more serious; he might feel uncomfortable about me revealing it to her due to the very new nature of what’s happening, plus the fact that he felt uncomfortable about their hookup even at the time and doesn’t like her; she might be pissed, and end our friendship or abuse him or me or make the whole thing public, which otherwise would not be on the cards. I also kind of feel like telling her when the whole thing is pretty sexually focused currently might come off as rubbing it in her face, and I’m worried about trying to define a situation to her that I haven’t even defined with him or myself.On the other hand, she’s my friend; I value our rebuilt and (until now) open and honest relationship, and I know I would feel gutted and also suspicious if a friend kept a secret like this from me for too long, particularly someone I trusted to be real with me. She does also have a happy long term partnership these days, so I wonder if that might mitigate things - but then I remember how much she resented Nella, and Nella wasn’t her friend. But then again, that was three years ago. But then again - I’m her friend. I’m just not sure what I should do.Ideally, this thing continues naturally, and Leonie is chill. Is there a way I can achieve that, or do I just cover it up completely, or do I blow it up completely with no attachment to outcome? Do I tell Sam before I tell Leonie or will that make things weirder?TL;DR I’m hooking up pretty consistently with an old friend Sam, who over 3 years ago hooked up with my friend Leonie, who caught feels at the time but is now in an LTR. Sam has no warm feelings towards Leonie and views their hookup as a mistake at best. Sam and I stayed mostly friends over the next few years while Leonie and I completely ended, then completely reforged, our friendship. Do I owe it to Leonie to tell her I’m hooking up with Sam, and if so, how?